


Hooking Up with Cowboys

by CastielsHeart



Category: Supernatural
Genre: 1970 Dodge Charger, Alternate Universe - Bar/Pub, Blow Jobs, Car Sex, Cowboy Dean Winchester, Cowboy Sam Winchester, Cunnilingus, F/M, Fluff and Smut, Nipple Play, Oral Sex, Pool & Billiards, Semi-Public Sex, Sex in the Impala, Vaginal Sex
Language: English
Status: Completed
Published: 2018-06-06
Updated: 2018-06-06
Packaged: 2019-05-18 20:42:57
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,523
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14859956
Author URL: https://archiveofourown.org/users/CastielsHeart/pseuds/CastielsHeart
Summary: Reader decides a night on the town with her friend Theodora is what she needs.  They get dressed up and go to a bar.  They meet sexy cowboy Sam and Dean.  Reader hits it off with Dean and her friend goes for Sam.  Fluff and Smut follow.





	Hooking Up with Cowboys

**Author's Note:**

  * For [Deans_Tiggermom](https://archiveofourown.org/users/Deans_Tiggermom/gifts).



> This is for my very good friend Deans_Tiggermom.

[](http://s1253.photobucket.com/user/Kelly_Ann_Tyler/media/Phototastic-6_6_2018_762301a2-7d42-4f37-b1ac-c73eb43e2d5b_zps6yt1dtkd.jpg.html)

 

You don’t normally go out to clubs, bars and such. Your Saturday nights usually consist of you curled up on the sofa with a soft blanket and a good book. Tonight though you have so much pent up energy that you just have to get out and do something.

You pop in the shower and use your best smelling body wash. You thoroughly shave your legs because who knows maybe you’ll have some strong hands on your thighs before the night is over. That thought brings heat to your cheeks and you have to turn the water a little colder to compensate. Once you’re out of the shower with a towel wrapped around, you stare into the mirror at your long red curly hair. “What to do… what to do?” you murmur to yourself.

You decide to drag out the hot rollers because you want big boucy curls as opposed to your tight unkempt looking ones. You apply base makeup while you wait for them to heat up. After an hour you have bouncy curly hair and some of the best makeup you’ve done in a while.

You decide on your short black skirt and a grey long sleeve sweater cut to slightly show your midriff. You put on your simple black choker and black thigh high boots. You take a long hard look in the mirror and you like what you see. Your simple but striking makeup compliments your outfit well.

[](http://s1253.photobucket.com/user/Kelly_Ann_Tyler/media/Phototastic-6_6_2018_8bd38eb7-9732-42c4-a416-4369706b7182_zpsgvq2pndg.jpg.html)

 

You’re ready but then the idea of going out alone causes your anxiety to build. The idea of who to drag along with you snaps into your head instantly. Your coworker and friend Theodora, Who everyone simply calls “Theo,” would not only be a welcome partner in crime, she would know the perfect place to go.

Grabbing your phone, you pull up your contacts to Theo. You’re confronted with a picture of Theo dressed as Maleficent from last Halloween. You have to admit she makes an awesome villain. She answers on the third ring, “Hey girl I didn’t expect to hear from you tonight. I thought you would be 200 pages deep in a novel by now.” Theo says with no preamble.

“Yeah that was my plan but I have decided a night out on the town is what I need. You were the first person I thought of to be my guide to the dark side.” You chuckle. Theo always claims she’s pure evil.

“This is fortuitous!” Theo exclaims. “I was about to head out to Benny’s Bar. There is a rodeo in town and the cowboys have been hanging out there. You know some tight jeans and a cowboy hat on a hot man would fit you just fine.”

“God, yes! Theo can you come get me?” you say sounding excited and anxious.

“Certainty, I’ll be there in fifteen minutes.” Theo says and the phone goes dead.

You’re vibrating with energy. You think to yourself, “This can go one of two ways. First it’s a night to remember to the end of time or my crazy friend, Theo, is going to get me arrested.”

You grab your sparkly black heart shaped clutch purse and sit on your porch to wait for Theo to arrive. It is a quiet warm starry night. Usually this would calm you but your heart is racing with anticipation of what this night might bring.

[](http://s1253.photobucket.com/user/Kelly_Ann_Tyler/media/C__Data_Users_DefApps_Windows%20Phone_AppData_INTERNETEXPLORER_Temp_Saved%20Images_imagesWJZE72L4_zpsdbqga9go.jpg.html)

Theo pulls up right on time and she is deck out. She is wearing a gorgeous short purple dress with black lace see through panels. She has on a wicked pair of black high heels with black skulls on them. Her long reddish brown hair with purple highlights is expertly styled. She wears a simple but elegant pair of earrings. God you wish you had the guts to pull off such an eccentric look. 

[](http://s1253.photobucket.com/user/Kelly_Ann_Tyler/media/Phototastic-6_6_2018_03cb22c5-9347-4358-84d1-fa93a33f9589_zpslpfn7yew.jpg.html)

Theo walks up to the porch with a smile on her face, “You ready chica?” 

“Absolutley.” You respond. When you stand Theo looks your wardrobe over.

“You look good. That outfit suits you well and man you have a good hand with makeup.” Theo complements.

You smile brightly at Theo because even though she is a little on the wild side, she always knows how to put you at ease. You admire her purple and white 1970 Dodge Charger for a brief moment before sliding in and you are off for a night on the town with your eccentric friend.

[](http://s1253.photobucket.com/user/Kelly_Ann_Tyler/media/C__Data_Users_DefApps_Windows%20Phone_AppData_INTERNETEXPLORER_Temp_Saved%20Images_imagesC2P80VY1_zps73qsgonz.jpg.html)

When you get to Benny’s Bar the lot is packed. There are a lot of trucks and vehicles of little interest but then you spot a black 1967 Chevy Impala. You have to run your hand down the side of this artwork of a car. She’s a beauty. Theo grabs your hand and pulls you toward the bar entrance saying, “Don’t fondle other people toys.” You laugh heartily. Theo can make the simplest statements dirty. 

When you walk in you both nod to Benny behind the bar. Benny is a tall man with a Cajun accent who is very mysterious. Many people have tried to get Benny to tell his story but no one has ever gotten him to talk. You don’t mind because Benny is a nice guy and we all have our demons we would rather not talk about. Benny is arguing with Anna. Anna is a local who really needs to spend a little time in a padded cell. She spends part of her time talking about what the voices in her head are telling her as well as spouting religious nonsense and the rest she’s is sloshed drunk trying to get into anyone’s pants. Looks like tonight is the latter. 

Theo goes to the opposite end of the bar from Anna. Last time those two had contact Theo broke Anna’s nose after she groped Theo’s boyfriend at the time right in front of her. Tonight though Theo is single and on the prowl. Her eyes are scanning the crowd looking for candidates. Her eyes stop scanning when she looks in the direction of the pool tables. “Look at those two tall hotties playing pool. I call dibs on the tallest one with the long hair.” Theo declares.

You follow where she’s indicating and yeah the tall one is nice looking but the other is breathtaking. He is slightly bow legged and wearing jeans that look like they have been painted on. He has the prettiest green eyes and pouty kissable lips. You think to yourself, “If I can get him this will be a night to write songs about.” You say out loud, “I’ll take the shorter no problem.” Theo looks at you and give you a devious smile. This is about to get interesting.

Theo and takes the lead and you’re okay with that. She walks up to the tall one and says, “Damn, I’d sale my soul for a chance to ride you.” You try to suppress the blush you know is already heating up your face. This is classic Theo you should have known.

“No need for that sweetheart. What your name gorgeous?” Mr. tall and handsome says. Damn that might be a record even for Theo.  
“My names Theodora but everyone calls me Theo and you?”

“My names Sam. Want to play a game of darts with me, Theo.” Sam asks looking Theo up and down like she is something to eat.

“Hell yes handsome. Show me how it is done.” Theo says making sure the innuendo is plain in her voice. Next thing you know they are on the other side of the room standing so close you can’t tell where one begins and the other ends.

You look over at green eyes and he smiling at you, “Your friend is a pistol.” He says to you.

“She sure is but that is a record even for her.” You reply.

“Well she is my brother, Sammy’s type, petit, cute and dangerous.” Green eyes says while watching you with veiled interest in his eyes. “I’m Dean by the way.” He reaches out a hand to take yours and you give him your name. He says it with his deep voice and you feel a shiver run down your spine.

“So darling do you know how to play pool?” Dean asks

“A little but I am not very good.” You admit.

“Come over here and I’ll show you my technique.” Dean flirts and, oh my gosh, is it doing things to you. He comes up behind you pressing closely into your back putting his hands over yours showing you the proper technique. His firm muscles pressed up against you, makes things tighten within you. 

You play quite a few rounds and you’ve totally forgotten about Theo. When you finally remember you look for her. You find her sitting at on table with Sam. His hand is so far up her dress that it could be considered public indecency. They say a few words to one another and then Sam seizes Theo’s lips in a passionate kiss. Dean follows your gaze and smiles. “Well they won’t be here much longer.” Dean chuckles.

“Damn it! Theo was my ride.” You say disappointed.

“Don’t worry sugar. I’ll take you home. I promise to be a gentleman.” Dean says giving a Boy Scout salute.

“I don’t know about the gentleman part. I was kind of hoping you could show me some more of your techniques.” You blurt out and you internally berate yourself because you think you sound silly. Then you look up at Dean and his pupils are blow and he licks his lips and you have to suppress a moan.

“Hold that thought.” Dean says as he grabs your hand and pulls you toward Theo and Sam. “Hey you guys seem to be having a good time.” Dean says when Sam and Theo finally part for air. “Why don’t you guys get out of here for some alone time. Theo, your beautiful friend here has agreed to let me escort her home.” Dean says gallantly. 

Theo looks over at you for confirmation. “Go on Theo. Have fun. I’ll call you tomorrow.” You reassure her.

“Alright chica.” Theo responds as Sam practically picks her up and carries her out of the bar.

Once they are gone Dean put his hand on your cheek and then seizes your lips like he is starving. He explores your mouth thoroughly with his tongue and you feel a little faint went he finally pulls back to give you air.

“Wow, you’re a good kisser.” you nervously divulge.

“Oh darling I plan on showing you just how good I can be. Shall we retire to somewhere more private?” Dean ask.

“Hell yes!” you say breathlessly.

Dean guides you to the parking lot right up to the 1967 Chevy Impala. He smiles, “may I introduce you to my baby.”

“This is yours. I saw it on the way in. A 1967 Chevy Impala is a beauty of a car. You keep her so well maintained. God she is exquisite.” You say not keeping you enthusiasm and excitement out of your voice.

“There is nothing sexier than a women that knows her cars.” Dean growls.

Next thing you know you’re lying in the backseat of the Impala with Dean muscular frame looming over you. He is kissing your neck and you let your hands roam over his broad chest. He takes a gentle bite of your ear and you can’t help but let out an explicit moan. “You make such beautiful noise.” Dean purrs. You answer with more moans because he now licking and nibbling at you neck again.

Dean lifts his head to look at you, “Darling how far do you want this to go.” He asks.

“All the way.” You say breathlessly.

“Damn baby.” Dean says as he grinds his groin into your thigh so you can feel just how happy he is with your response. You both decide at the same time you have to many cloths on. You’re not really sure how you managed to get each other’s cloths off so fast in the small confines of the backseat of the Impala but you manage it.

Dean takes your left nipple into his mouth and gently nibbles and sucks until it is so sensitive you cry out. He takes the right and repeats the process. His ministrations have you so wet you decide to retaliate by grabbing his hard length and start jacking him off painfully slow because two can play this game. 

You force him to switch positions letting you on top. You straddle his lower thighs and bend down and swipe your tongue from the base of his cock to the tip in an agonizing slow motion. Dean looks up at you and says, “Baby why do you have to be so cruel.” You smile deviously back down at him and then you lick your tongue across his weeping slit. He groans and arches up searching for the warmth of your mouth. You can’t help but giggle at his eagerness. 

You take pity on him and take his long hard length into your mouth all the way to the base. You still for a moment to let your throat get used to the intrusion then you bob up and down establishing a brutal pace. You continue to you feel he is on the edge and then you slide off his dick with a wet pop. Dean moans and writhes, “Please Baby!”

“It’s my turn green eyes.” You say with your wrecked voice.

Dean eyes light up, “Hell yeah baby! Come up here and sit on my face.” Dean commands.

He doesn’t have to tell you twice. You crawl up his body and lower yourself down slowly. Dean starts doing things to you with his tongue and you throw your head back and moan like a porn star and you absolutely don’t care. When he has you close you tap him twice to let him know to stop. You slide back down to sit across his chest. “Do you have a condom?” you ask.

“Sure do darling.” He retrieves it and you put it on. You stoke him a few times before raising up and lowering yourself down onto him. It feels wonderful and then you start to move and it feels fantastic. You set a slow pace and Dean growls, “flip for me.” He orders. 

Next thing you know Dean strong muscle frame is over you pounding you mercilessly. He’s is chasing his orgasm and yours as though he is being chased by Lucifer himself. You feel the heat and the pressure building between your legs. You are so close and by the sounds Dean is making so is he. Dean make a very explicit moans and starts to stutter in his pace. It is with a very deep and quick thrust that he pushes you over the edge. You feel your muscle tighten around his shaft and he leans up seizing you mouth and screaming his release into your mouth.

As you mind gives over to the post coital haze you think, “Man this was so much better than reading a book.”


End file.
